Benzoyl chloride → HCID 54244647, compound

HRID 1248340Notes

Reaction equation

HRID 1248340 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]([C:9]1[C:12]2[CH:13]=[C:14]([O:17]C)[CH:15]=[CH:16][C:11]=2[CH:10]=1)=[O:8].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:5][O:6][C:7]([C:9]1[C:12]2[CH:13]=[C:14]([OH:17])[C:15]([C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][C:11]=2[CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 541184135-Methoxybenzocyclobutene-1-carboxylic acid methyl ester

Product 1

HCID 54244647HCID 54244647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

95.7 g of finely pulverised aluminium chloride are suspended in 180 ml of absolute methylene chloride. While stirring and cooling, 35 g of 5-methoxybenzocyclobutene-1-carboxylic acid methyl ester, dissolved in a small amount of methylene chloride, are added dropwise in such a manner that the temperature remains below 30°. At the same temperature, 50.5 g of benzoyl chloride are added dropwise thereto and the whole is subsequently heated at reflux for 4 hours. After cooling, the reaction mixture is poured onto 600 g of ice. The organic phase is separated off and the aqueous phase is extracted 3 times with 150 ml of methylene chloride each time. The combined organic phases are washed once with 250 ml of water, dried over magnesium sulphate and concentrated by evaporation. The excess benzoyl chloride is distilled off under a high vacuum and the residue is crystallised from ether/petroleum ether. 4-benzoyl-5-hydroxybenzocyclobutene-1-carboxylic acid methyl ester is obtained in the form of yellow crystals having a melting point of 75°-76°.

Workup

  1. temperaturecooling
  2. additionare added dropwise in such a manner that the temperature
  3. customremains below 30°
  4. temperaturethe whole is subsequently heated
  5. temperatureat reflux for 4 hours
  6. temperatureAfter cooling
  7. customThe organic phase is separated off
  8. extractionthe aqueous phase is extracted 3 times with 150 ml of methylene chloride each time
  9. washThe combined organic phases are washed once with 250 ml of water
  10. dry with materialdried over magnesium sulphate
  11. concentrationconcentrated by evaporation
  12. distillationThe excess benzoyl chloride is distilled off under a high vacuum
  13. customthe residue is crystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-f5d0c0120d2c48fe8399951fffd24f06
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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